It’s so hard to say goodbye, but it’s time to go. On May 17, AMC’s Mad Men will be taking a bow and exiting stage left, most likely leaving us with both more questions than answers, and pondering the strengths and weaknesses of television’s most complicated characters.

But one of the most important characters on Mad Men is the music. Each episode uses songs from the era to illustrate things that the characters, dialogue, setting and plot may not convey. Sometimes music foretells of things to come. Sometimes it ties up what has just unfolded. But whatever its purpose, Mad Men would not be Mad Men without the music.

SiriusXM’s Lou Simon, programming director extraordinaire of ’60s on 6, took a look at both the story arch of each season as well as the months it covered, and picked the songs he thought most reflected what the characters and the country were going through at the time.

Season 1: March – November 1960

When we were first introduced to Mad Men, you could sense the beginning of the end of 1950s idealism. There were hints of what was to come with beatniks and other counterculture, but overall it was the last fumes of ’50s America, setting the stage for times that were a changin’.

Itsy Bitsy Teenie Weenie Yellow Polka Dot Bikini – Brian Hyland (July 1960)
The ANTHEM of the summer of 1960, this song heralded in the era of the more exposed woman on the beach … which Don Draper MUST have noticed!Theme From The Apartment – Ferrante & Teicher (September 1960)
The first big hit for this piano playing duo was the theme from a Jack Lemmon movie about an apartment used by businessmen to have affairs. Sounds right up Don’s alley.

Season 2: February – October 1962

Don’s infidelity and marital problems with his wife, and Peggy’s ascent from secretary to copywriter illustrated a shift in values as well as in gender roles. Not to mention more signs of a new youth culture. The final episodes of this season culminated in the Cuban Missile Crisis.

Twistin’ the Night Away – Sam Cooke (March 1962)
Finally, a dance for people who don’t know how to dance! The lyric about the older guy dancing with the younger “chick in slacks” … well … you know the rest.If I Had a Hammer – Peter Paul & Mary (October 1962)
Their first top 10 hit, it’s a Pete Seeger song that has hootenanny written all over it. Beatniks rule! Greenwich Village lives!!!

Season 3: April – December 1963

This season chronicles the death throes of the “Camelot Era” with a lot of ends in the characters’ lives. Don’s marriage ends, Sterling Cooper ends and it’s all mixed up in a stew of madness and passion. Kennedy dies, the Beatles are about to land in New York and a lot of the characters’ idealized post-war era lives are shattering, forcing them to ask, “Who am I?” and “Who do I want to be?” but also forcing them to face some harsh realities about themselves. This season is really when the show crosses the cultural line from the ’50s to the ’60s.

Days of Wine and Roses – Andy Williams (April 1963)
Andy’s version of this theme to a Jack Lemmon movie (again) was as kitchy as the era itself, and the movie was all about the excess and depravity that a marriage can handle!Wives and Lovers – Jack Jones (December 1963)
It’s the most jet-set, misogynistic song of all time! And a guilty pleasure to this day. “Day after day, there are girls in the office … and men will always be men …”

Season 4: November 1964 – October 1965

Season 4 kicks off at the new, way more modern advertising agency, Sterling Cooper Draper Price. Don is going through an identity crisis, falling into darkness as a bachelor adrift in the city. It’s all about casual sex and lots of booze for Don. But by the end of the season, he’s met and is set to marry his much younger secretary Megan. On the other hand, Peggy continues to rise up the ladder, putting her career before her personal life, spearheading a big campaign, and showing a small but significant rise of women in the workforce.

Oh, Pretty Woman – Roy Orbison (October 1964)
He’s doing the growling … but SHE knows she’s the one in control. Enter the new woman.The “In” Crowd – Dobie Gray (February 1965)
Struggling with your own identity, and finding a group to get lost in can sometimes help. “If it’s square, we ain’t there.” Love it.

Season 5: May 30, 1966 – Spring 1967

Don puts his focus on his new marriage over his work, causing resentment from Peggy and his other employees. A new, smart male hire challenges Peggy, revealing the glass ceiling above her. And Roger experiments with LSD, which has a profound impact on him. All the characters have realizations about themselves.

Season 6: December 1967 – November 1968

In this season, all the characters are struggling to adjust to the ongoing counterculture movement around them. A sense of dread hangs over everything with subtle symbols foreboding a darker time of the ’60s. Throughout there are images of violence, and Don disappoints both in his personal and professional life, coming off as not much more than a washed-up loser with his lying and alpha-male entitlement coming home to roost. This is the period when both RFK and MLK Jr. were assassinated, and it was a catastrophic year for Don Draper as well.

Daydream Believer – The Monkees (December 1967)
This song, written by folkie John Stewart, tells of dashed dreams, a glittery past and good dose of, “How did I get here and who am I anyway?”MacArthur Park – Richard Harris (July 1968)
Over seven minutes long, with obtuse lyrics filled with symbolism and an almost spoken vocal by the Irish actor, this unlikely hit was huge all summer. And a reminder that conventions were changing and the rules were being ripped up and re-written as we moved along.

Season 7, Part I: January 1969 – July 1969

The party’s over and the truth is finally catching up with all the people who make a living selling false hope. The characters are forced to deal with the shattered remains of many of their decisions and sift through to see what can be fixed and what is irreparable.

I Started a Joke – Bee Gees (February 1969)
“ … which started the whole world crying”. Are they talking about the ad industry? Probably not … but they might as well have been.Hair – The Cowsills (May 1969)
It’s a new day … even for The Cowsills. Nudity on Broadway. What’s next? A female CEO?